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Vacation Rentals & Homes in Sag Harbor

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159 homes

Beech Tree Cottage

Sag Harbor cottage

2 bedrooms / 1 bathroom / sleeps 4

“Loved this place” This is the perfect little getaway for those who wish to avoid the pretentiousness of East Hampton and Southampton and still enjoy everything that the Hamptons has to offer. Best things - very cute little cottage. Good enough space with off-street parking. The ability to walk into Sag Harbor village in a few mins is a massive plus. Stephen and Emma are so nice and great neighbors if there are any issues. Would definitely recommend this place to anyone.

Price per night from

$687

East Hampton/Sag Harbor Village Fringe

Sag Harbor house

6 bedrooms / 7 bathrooms / sleeps 12

Price per night from

$3,435

ROMANTIC LUXURY RETREAT WITH POOL & WATER VIEWS, 1 MILE FROM SAG HARBOR VILLAGE

Sag Harbor house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$985

Sag Harbor Village Fringe, Great Location

Sag Harbor house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$2,290

Hampton's Paradise sag Harbor, Southampton

Sag Harbor house

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$1,145

Village traditional on a quiet cul de sac

Sag Harbor house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 2 hours 53 minutes

Price per night from

$1,276

Beautiful Guest House Waits For You - Hamptons - Sag Harbor

Sag Harbor guest house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$453

The Seashell House

Sag Harbor house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$974

no longer avail property Sold !

Sag Harbor cottage

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,031

Great 4 bedroom family home walking distance to the beach and village

Sag Harbor house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,145

Great rentals within 20 miles that match your search

North Fork House with Private Beach Access

East Marion house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$343

Ready for Summer 2021

Southampton house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,718

PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES

Southold house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$430

Fantasy Bay Front Country French Villa

Southampton villa

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$2,290

Hip & Stylish East Hampton Getaway

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 6

“Wonderful stay” Me, my husband and our daughter rented this nice house for a week. It was really great, Patricia was so nice and helpful from the start when we wanted to rent it until we left. The house is light, nicely furnished, comfortable beds with nice linen. The kitchen is really well equipped, also with an espresso machine so you can enjoy good coffee at home. We stayed by the house a lot and enjoyed the deck with the grill and the nice pool with the floating sunchairs. We liked that it had all the trees and it's in a quiet area. It's only 10-15 min. drive to East Hampton town and to the beaches nearby. We can really recommend this house and we would love to come back soon.

Price per night from

$409

Perfect Hamptons Rental with Pool and Tennis

Bridgehampton house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$1,661

Hampton Accommodations 3 / FREE BIKE RENTALS

East Hampton b&b

1 bedroom / 2 bathrooms / sleeps 2

Price per night from

$315

Hampton accommodations 2

East Hampton b&b

1 bedroom / 2 bathrooms / sleeps 2

Price per night from

$287

Romantic Luxury Winery Apartment

Jamesport apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$287

Majestic Southampton Waterfront Estate

Southampton villa

7 bedrooms / 5 bathrooms / sleeps 18

“Best alternative to Fire Island” My partner and I wanted to try something new, we originally always go to Fire Island and although we will always love that place, I can't express how expensive it is just to go for a weekend with friends not to mention that we can't help but feel stranded in a way (we don't drive) because once the ferry leaves, that's it! You will be staying whether you want to or not. I would have never thought that I would find a house of this size, with amenities such as linens, towels, beach chairs, hot tub, and pool included for such a reasonable price at the Hamptons none the less...I thought it had to be a mistake, I literally had to call to confirm the rates. The owner was very prompt in her responses whether it would be through phone and or email, and she definitely went out of her way to make sure we were properly accommodated as well as gave awesome recommendations to nearby shops and restaurants. I never had such a pleasant and smooth experience. It was a one, two, three transaction and was very pleased with the outcome, will be coming back next year for sure!

Price per night from

$1,390

Great Rates in 2019- No Increases In Rates and Over Holiday Weeks

Hampton Bays house

3 bedrooms / 2 bathrooms / sleeps 6

“Hamptons” Dear Jackie and al, we had a wonderful time in your house. The service was perfect. We had everything in the house we needed. It is a in nice area . There are shops and restaurants near by. Thanks for everything Ina and family

Price per night from

$458

Classic Hamptons Home in beautiful Water Mill - Minimum 2 week rental

Water Mill house

5 bedrooms / 4 bathrooms / sleeps 13

Price per night from

$1,718

Waterfront Southampton Gem! Sailboat On Grounds - Travertine patio and Hot Tub

Water Mill house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$779

Spectacular Family Resort in Hampton Bays, NY

Hampton Bays house

7 bedrooms / 5 bathrooms / sleeps 18

“Hamptons Heavenly Honeymoon” My fiancé and I wanted to go somewhere amazing for our honeymoon. We decided that we wanted to spend our honeymoon in the Hamptons. We spent two lovely weeks in august of 2013 at this lovely home. There is nothing bad that I could say about this house. It was spacious, clean, well kept, and well decorated. This house was in the perfect location. It was close enough to the town of Hampton Bays but also close enough to Riverhead. The owner of the house was very cooperative, if we had a question she would answer all of them without hesitation. During the stay my fiancé and I spent most of our time outside. It was so quite and peaceful. We would sit by the pool and enjoy a glass of wine. I would highly recommend this house to anybody. My fiancé and I were talking and once we start a family we are going to make coming to this house a tradition.

Price per night from

$819

Cutchogue Beach Cottage

Cutchogue cottage

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$172

Waterfront Condo C204 at The Cliffside Resort

Greenport apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 4 minutes

Price per night from

$458

East Hampton shingle style home

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$859

Hamptons Lofty Beach Barn - Pet Friendly

Water Mill house

4 bedrooms / 2 bathrooms / sleeps 12

Responds fast! avg. 1 hour 38 minutes

Price per night from

$1,718

Private Waterfront W Beach, New Renovation

Southold house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$831

Montauk Ocean View Retreat-Rental Registry #16-950

Montauk house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,145

Amagansett Estate 3 BR 60ft Pool

Amagansett house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$1,374

Newly remodeled mid century modern

East Hampton house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$573

Quaint Seaside Retreat With Full Gym

Hampton Bays house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 2 hours 6 minutes

Price per night from

$1,374

Beautiful Estate home in the Hamptons, New York

Water Mill villa

7 bedrooms / 7 bathrooms / sleeps 10

Price per night from

$6,870

Amagansett Estate 5 Bedroom 60ft Pool

Amagansett villa

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,603

Bishops Pond Southampton NY

Southampton townhouse

4 bedrooms / 10 bathrooms / sleeps 8

Price per night from

$147

SOUTHAMPTON NEW YOK LUXURY RENTAL

Southampton house

4 bedrooms / 11 bathrooms / sleeps 8

Price per night from

$2,045

Amagansett Estate 4BR 60ft Pool

Amagansett manor house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,203

Viewing 38 of 159
rentals in Sag Harbor

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About Sag Harbor

Sag Harbor is historic hamlet with a real maritime vibe. If you're hoping to experience a unique culture, a world away from normal life, this quirky little resort is certainly an option for you. FlipKey has a great selection of homes to choose from. Book today to secure your Sag Harbor stay.

About Sag Harbor

Sag Harbor is a small village located in Suffolk County, New York and has an extremely rich history which tourists are still eager to discover to this day. The first settlers arrived in the 1600s, and by the 1800s became one of the busiest ports in the world, still famed for its marine heritage.

Thanks to years of preservation and care, the majority of the architecture from the 18th and 19th centuries still remains, which include the likes of Greek Revival Houses and Victorian homes for the rich.

The area within and around Sag Harbor has a great deal of nature, as well as many endangered species such as the eastern tiger salamander. Nature preserves in Sag Harbor include Barcelona Neck Preserve, Sag Harbor Woods Preserve and Cilli Farm. Here, you may be able to spot mammals such as the white-tailed deer, red fox, eastern coyote, mink and a variety of bat species.

What to do

If you're interested in seeking out the cultural sights of the region, why not visit the Sag Harbor Fire Department Museum? Built in 1833, this building was created due to four severe blazes which broke out in the 1800s. Now, it serves as a museum and displays a wide range of fire equipment and other interesting pieces to view.

There's also the Sag Harbor Whaling and Historical Museum, located in an 1845 building. Here, you can explore displays of marine heritage with boat displays, models and furnishings as well as special exhibits.

If you're looking to see more of the area, you may decide on taking a trip to the local rocky beach known as Foster Memorial Beach. Or, if you're looking for a taste of adventure, the most popular activities here are kayaking and boating out to Long Island. You will enroll in a two-day course which is ideal for beginners.

Top Sea Harbor travel tips

If you're looking to find a cheaper alternative than traveling to Suffolk County by plane, there is a bus which departs from Manhattan and will drop you off at Sag Harbor. The round-trip fare is just $53 per person.

It would be advised to have a car to get around Sag Harbor, due to the remoteness of the town. This would also be advised if you plan on exploring the other local areas or are hoping to venture out further.

The peak season to travel to this particular region is between May-September, so always book far in advance.

Sag Harbor is the idealized quiet town you may have always wished to escape to; especially if you live in a busy city. Here, you can explore history culture and even try your hand at water-sports if you dare... Book your Sag Harbor vacation rental with FlipKey to start your next trip.

Top Destination reviews

Beech Tree Cottage
A home from home

I stayed with two friends, their 15 month old and two week old in Beech Tree Cottage in June and we had a great time. The cottage has a very comfortable, cosy feel to it and had everything we needed. The location is perfect as we were close to town and it was easy to get around by car to explore the area. The owners are keen to point out that there is no bath and that the spiral staircase is narrow, but this didn't prove a problem for us for a two-night stay. We were only sorry not to meet our hosts during our short stay. Highly recommended.see more

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